The present invention provides methyl phenyl pentanol derivatives defined according to the generic structure: ##STR2## wherein R represents hydrogen or acetyl, an economical process directed towards synthesizing said methyl phenyl pentanol derivatives and organoleptic uses thereof for augmenting or enhancing the aroma or taste of perfume compositions, colognes, perfumed articles, foodstuffs, chewing gums, toothpastes, medicinal products and chewing tobaccos.
There has been considerable work performed relating to substances which can be used to impart (or alter, modify or enhance) fragrances and aromas and/or tastes to (or in) perfume compositions, colognes, perfumed articles, foodstuffs, chewing gums, chewing tobaccos, medicinal products and toothpastes. These substances are used to diminish the use of natural materials, some of which may be in short supply and/or to provide more uniform properties in the finished product.
Powerful, long-lasting, stable green, grapefruit-like, nootkatone-like, animalic, leathery, vetiver-like, olibanum, musky and floral aromas are highly desirable to many types of perfume compositions, perfumes and perfumed articles, particularly herbal fragrances and herbal fragranced soaps and detergents.
Floral, green, weedy, fruity, grapefruit, galbanum-like, nootkatone-like, oriental and green pepper-like aroma and taste nuances are highly desirable in the creation of flavors for foodstuffs, chewing gums, toothpastes, medicinal products and chewing tobaccos.
Methyl phenyl pentanol derivatives are known for use in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes. Thus, U.S. Pat. No. 4,206,090 issued on June 3, 1980 discloses the compound having the structure: ##STR3## for use in augmenting or enhancing the "rose" aroma of perfume compositions, colognes and perfumed articles. This compound is also disclosed in Beilstein Vol. E III 6(1997) at H6, 551. Other homologues and isomers of methyl phenyl pentanol derivatives also are known to have rosy fragrance aroma nuances. These methyl phenyl pentanol derivatives known in the prior art have the structure: ##STR4## (at Chem. Abstracts 58 2420d and 60 15711a); the structure: ##STR5## (at Chem. Abstracts 78 42690r (abstract of article by Khalaf in the Journal of Organic Chemistry); the structure: ##STR6## (at Chem. Abstracts 76 126027b (1976) abstract of article by Winstein in J. Org. Chem.); the structure: ##STR7## disclosed in Dutch Patent No. 59422; the structures: ##STR8## disclosed in Beilstein E III 6 (1997) at H6-551; and the structure: ##STR9## disclosed in Beilstein E III b-1998 at H6 551-2 which is an abstract of Bogert et al JACS 56 (1934) 959 et seq.
German Offenlegungsschrift No. 3,103,268 published on Aug. 26, 1982 discloses the compound having the structure: ##STR10## prepared from the precursor compounds having the structures: ##STR11## German Offenlegungsschrfit No. 3,103,268 is abstracted at Chem.Abstracts, Volume 97:181968t (1982).
The subject matter of the instant application is disclosed in U.S. Pat. No. 4,458,699 issued on July 10, 1984 and filed on Feb. 11, 1982 as application for U.S. Letters Patent, Ser. No. 347,995. The subject matter claimed herein was conceived of and reduced to practice prior to the filing date of said U.S. Pat. No. 4,458,699, that is, prior to Feb. 11, 1982.
None of the methyl phenyl pentanol derivatives of the prior art have aroma or taste profiles even remotely similar to the aroma or taste profiles of the methyl phenyl pentanol derivatives of the instant application defined according to the structure: ##STR12## wherein R is hydrogen or acetyl. The methyl phenyl pentanol derivatives of my application defined according to the structure: ##STR13## have unexpected, unobvious and advantageous organoleptic properties compared with the methyl phenyl pentanols of the prior art.